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Copper-catalyzed conjugate addition of in situ formed alkyl boranes to α,β-unsaturated ketones

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Abstract

Conjugate addition of in situ formed organometallic reagents to α,β-unsaturated carbonyl compounds provides an efficient way to generate new C–C bonds. We show optimization of the copper-catalyzed conjugate addition of alkylboranes, which were formed directly in the reaction mixture by hydroboration of alkenes. We have improved the reaction conditions by employing “greener”, less hygroscopic, and higher boiling solvent, 2-methyltetrahydrofuran. We have also broadened the scope of the reaction. Furthermore, chiral ferrocenyl carbene ligands were assessed in the enantioselective version of the transformation with medium enantioselectivity 67:33 e.r.

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Acknowledgements

This work was supported by the Slovak Research and Development Agency under contract no. APVV-0321-12.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Ilkovičova 6, 842 15, Bratislava, Slovakia

    Bernard Mravec, Kristína Plevová & Radovan Šebesta

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  1. Bernard Mravec
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  2. Kristína Plevová
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  3. Radovan Šebesta
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Correspondence to Radovan Šebesta.

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Mravec, B., Plevová, K. & Šebesta, R. Copper-catalyzed conjugate addition of in situ formed alkyl boranes to α,β-unsaturated ketones. Monatsh Chem 150, 295–302 (2019). https://doi.org/10.1007/s00706-018-2309-5

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  • DOI: https://doi.org/10.1007/s00706-018-2309-5

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